1-Methylhomopiperazine → 2-[4-(4-Methylhexahydro-1,4-diazepin-1-yl)piperidin-1-ylcarbonyl]amino-N-(5-chloropyridin-2-yl)benzamide

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A solution of N-(5-chloropyridin-2-yl)-2-(4-oxo-piperidin-1-ylcarbonyl)aminobenzamide (100 mg, 0.268 mmol) and 4-methyl(hexahydro-1,4-diazepine) (0.03 mL, 0.241 mmol) in 10% acetic acid in methanol (2.2 mL) was treated with sodium cyanoborohydride (20 mg, 0.268 mmol). After 15 h, the mixture was loaded onto a SCX column, which was pretreated with a solution of 5% acetic acid in methanol. The column was eluted with methanol followed by 2 N ammonia in methanol. The eluent was concentrated to afford title compound.

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